Sideshow has said in the Q&A for the 17th that he will NOT come with a helmet.
Maybe at a later date-an accessory perhaps??maybe another helmet head like Leia Boushh??thou probably unlikely.
I'm sure the Clone helmet head for a Clone Trooper down the road will use the exact same neck joint, so when that comes out, you could just put that head on the Obi-Wan figure, though it means hunting down an extra head or buying a Clone for parts.